YOUR NEXT GUADALAJARA ESCAPEBest fares checked Sep 27, 2026Seven-night round trip · one adult · USD · sampled fares
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Prices may change. Select and confirm the full itinerary with the booking provider. Dates can differ between airport cards.

CHICAGO → GDL

Cheap flights from
Chicago to Guadalajara.

A great Guadalajara trip starts with a fare worth finding. Compare the latest samples below, then join our upcoming free newsletter to get standout Chicago flight finds in your inbox.

Last checked Sep 27, 20261 adult · Economy · USDSources & coverage
Lowest recently sampled round trip
$284
Google Flights Compare on Skyscanner ↗

Same airports & dates. Each provider checks its own current prices.

ORD → GDL · Jan 23–Jan 30
Outbound and return checked.

A LOWER FARE. A BIGGER TRIP BUDGET.

What could a better fare change?

Spend more on being in Guadalajara, and less on getting there. These are real examples from our research—the reason it pays to keep an eye on the fares.

FLEXIBLE TRAVEL DATES$468 less

62% below the priciest date sample

$284 for Jan 23–Jan 30, 2027, compared with $752 for Dec 28–Jan 4, 2027.

12 seven-night date pairs from ORD to the same arrival-airport set (GDL). Lowest returned fare per date pair; checks within 24 hours. Airlines, stops and ticket conditions can differ. A travel-date comparison, not a booking-time prediction.

Explore the cheaper date samples ↗
WHY WATCH THE PRICE?23% price gap

$78 between this search’s high and low

The same dated search ranged from $261 to $339 across 61 historical price observations.

ORD → GDL · Jan 23–Jan 30, 2027. Google Flights history covers Jul 29, 2026–Sep 27, 2026. The percentage is the low below the high. This does not prove when you should book or what subscribers will save.

See the price history ↗
OUR LOWEST RECORDED FARE$284

The lowest seven-night fare in our archive

ORD → GDL · Jan 23–Jan 30, 2027. Recorded Sep 27, 2026.

Our archive starts Sep 27, 2026 and contains 179 seven-night fare observations for this route. Search fare; return may require confirmation. This is our record, not an industry-wide all-time low or a current offer.

How we keep fare records ↗
START WITH THE RIGHT AIRPORT

O’Hare or Midway?

Same dates: Jan 23–Jan 30. Same arrival airports: GDL.

ORD
O’Hare International
$284

Nonstop outbound

MDW
Midway International
$465

1 stop outbound

$181 separates the lowest and highest airport sample for these dates. These are search-result fares for seven-night trips. Flight times, stops and baggage can differ. Ground transport is excluded.

Across 12 matched date pairs in this sample, ORD had the lowest airport fare 12 time(s); MDW had the lowest airport fare 0 time(s). Ties count for each airport. This describes the sampled dates only.

YOUR AIRPORT, YOUR MATH

Which airport wins for you?

A cheaper ticket can come with a pricier ride. Add your own round-trip transport estimate to the matched fares.

ORD

Flight sample $426

$426fare + transport
MDW

Flight sample $658

$658fare + transport

Add your transport estimates to compare your total.

One adult, economy, USD. The two fares use identical dates and arrival-airport sets, checked within 24 hours. Transport starts at $0 because we don’t know your starting point. Baggage and other extras are excluded. Prices and itineraries can differ.

A FEW NUMBERS TO TRAVEL BY

Guadalajara, by the flight.

4h 4m

Fastest sampled outbound

ORD → GDL, Oct 11. Nonstop.

7

Airlines in the mix

Across 24 seven-night airport/date searches. Includes connecting carriers.

12

Travel windows sampled

Lowest: $284, Jan 23–Jan 30 from ORD.

2 / 2

Origins with nonstop samples

MDW, ORD in these outbound results. This is not a full schedule.

Derived from the current seven-night observations on this page. Outbound times describe the outbound journey only; fare amounts are round-trip search results. See sources and coverage.

A LITTLE FLEXIBILITY CAN HELP

Compare upcoming travel dates.

Lowest fare in each sampled departure month. Seven-night trips only.

Swipe to see more months →

Oct 26Nov 26Dec 26Jan 27Feb 27Mar 27Apr 27May 27Jun 27Jul 27

Tap a bar to see the dates, airports and check time behind that sample.

Read the chart as a data table
Departure monthLowest sampleDate pairs
2026-10$4261
2026-11$2881
2026-12$2882
2027-01$2841
2027-02$2871
2027-03$3131
2027-04$4261
2027-05$4461
2027-06$4292
2027-07$5601

Sampled dates, not a complete fare calendar. Each month can have different date coverage. This chart describes future travel dates, not past price movements.

THE DETAILS BEHIND THE PRICE

Find a fare worth your next trip.

Prices checked within seven days. Use the filters to find a trip that fits.

Round-trip search fares · 36 representative results · return verification marked individually
Dates / airportsAirline / outboundRound tripCheck price
Jan 23–Jan 30ORD → GDL · 7 nightsVivaNonstop · 4h 30m$284Return also checkedChecked Sep 27Google Skyscanner ↗
Itinerary

ORD → GDL
VB 547 · 2027-01-23 25

GDL → ORD
VB 546 · 2027-01-30 18:46

Feb 18–Feb 25ORD → GDL · 7 nightsViva1 stop · 7h 9m$287Select return to confirmChecked Sep 27Google Skyscanner ↗
Nov 6–Nov 13ORD → GDL · 7 nightsViva1 stop · 8h 21m$288Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9ORD → GDL · 7 nightsViva1 stop · 8h 21m$288Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → GDL · 7 nightsVivaNonstop · 4h 24m$293Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → GDL · 7 nightsViva1 stop · 8h 26m$297Select return to confirmChecked Sep 27Google Skyscanner ↗
Mar 15–Mar 22ORD → GDL · 7 nightsVivaNonstop · 4h 24m$313Select return to confirmChecked Sep 27Google Skyscanner ↗
Mar 15–Mar 22ORD → GDL · 7 nightsViva1 stop · 8h 18m$316Select return to confirmChecked Sep 27Google Skyscanner ↗
Nov 6–Nov 13ORD → GDL · 7 nightsVivaNonstop · 4h 14m$340Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9ORD → GDL · 7 nightsFrontierVolaris1 stop · 16h 24m$377Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → GDL · 7 nightsFrontierVolaris1 stop · 12h 31m$400Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → GDL · 7 nightsVolarisNonstop · 4h 23m$414Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 11–Oct 18ORD → GDL · 7 nightsVivaNonstop · 4h 10m$426Select return to confirmChecked Sep 27Google Skyscanner ↗
Apr 10–Apr 17ORD → GDL · 7 nightsVivaNonstop · 4h 24m$426Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 1–Jun 8ORD → GDL · 7 nightsVivaNonstop · 4h 24m$429Select return to confirmChecked Sep 27Google Skyscanner ↗
May 6–May 13ORD → GDL · 7 nightsVivaNonstop · 4h 24m$446Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → GDL · 7 nightsFrontierVolaris1 stop · 11h 7m$460Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30MDW → GDL · 7 nightsFrontierVolaris1 stop · 8h 22m$465Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → GDL · 7 nightsAeromexicoNonstop · 5h 0m$470Select return to confirmChecked Sep 27Google Skyscanner ↗
Jan 23–Jan 30ORD → GDL · 7 nightsAeromexico1 stop · 7h 53m$470Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → GDL · 7 nightsAeromexicoNonstop · 5h 0m$470Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25ORD → GDL · 7 nightsAeromexico1 stop · 8h 11m$470Select return to confirmChecked Sep 27Google Skyscanner ↗
Feb 18–Feb 25MDW → GDL · 7 nightsDeltaAeromexico2 stops · 21h 10m$485Select return to confirmChecked Sep 27Google Skyscanner ↗
May 6–May 13MDW → GDL · 7 nightsDeltaAeromexico2 stops · 22h 1m$485Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 27–Jul 4ORD → GDL · 7 nightsAmerican1 stop · 14h 47m$499Select return to confirmChecked Sep 27Google Skyscanner ↗
Mar 15–Mar 22MDW → GDL · 7 nightsDeltaAeromexico2 stops · 21h 17m$509Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 1–Jun 8MDW → GDL · 7 nightsDeltaAeromexico2 stops · 17h 0m$530Select return to confirmChecked Sep 27Google Skyscanner ↗
Apr 10–Apr 17MDW → GDL · 7 nightsDelta1 stop · 8h 5m$534Select return to confirmChecked Sep 27Google Skyscanner ↗
Jul 23–Jul 30ORD → GDL · 7 nightsAeromexico1 stop · 8h 30m$560Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 2–Dec 9MDW → GDL · 7 nightsVolarisNonstop · 4h 20m$577Select return to confirmChecked Sep 27Google Skyscanner ↗
Oct 11–Oct 18MDW → GDL · 7 nightsVolarisNonstop · 4h 7m$658Select return to confirmChecked Sep 27Google Skyscanner ↗
Nov 6–Nov 13MDW → GDL · 7 nightsVolarisNonstop · 4h 20m$658Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 28–Jan 4ORD → GDL · 7 nightsVivaNonstop · 4h 30m$752Select return to confirmChecked Sep 27Google Skyscanner ↗
Jul 23–Jul 30MDW → GDL · 7 nightsDelta1 stop · 6h 25m$793Select return to confirmChecked Sep 27Google Skyscanner ↗
Dec 28–Jan 4MDW → GDL · 7 nightsVolarisNonstop · 4h 20m$901Select return to confirmChecked Sep 27Google Skyscanner ↗
Jun 27–Jul 4MDW → GDL · 7 nightsDelta1 stop · 6h 25m$988Select return to confirmChecked Sep 27Google Skyscanner ↗

Prices can change. Cabin baggage and checked bags are not assumed included. Confirm the complete itinerary, airline fare rules and final price on the booking site.

ONE SEARCH, OVER TIME

How this search’s price moved.

ORD → GDL · Jan 23–Jan 30, 2027

Jul 29, 2026$261–$339Sep 27, 2026
Read the historical observations
Observation datePrice
Jul 29, 2026$302
Jul 30, 2026$309
Jul 31, 2026$310
Aug 1, 2026$302
Aug 2, 2026$310
Aug 3, 2026$310
Aug 4, 2026$311
Aug 5, 2026$311
Aug 6, 2026$320
Aug 7, 2026$338
Aug 8, 2026$339
Aug 9, 2026$339
Aug 10, 2026$320
Aug 11, 2026$318
Aug 12, 2026$318
Aug 13, 2026$318
Aug 14, 2026$319
Aug 15, 2026$321
Aug 16, 2026$320
Aug 17, 2026$269
Aug 18, 2026$280
Aug 19, 2026$300
Aug 20, 2026$310
Aug 21, 2026$311
Aug 22, 2026$311
Aug 23, 2026$311
Aug 24, 2026$271
Aug 25, 2026$276
Aug 26, 2026$275
Aug 27, 2026$275
Aug 28, 2026$275
Aug 29, 2026$275
Aug 30, 2026$275
Aug 31, 2026$286
Sep 1, 2026$286
Sep 2, 2026$286
Sep 3, 2026$286
Sep 4, 2026$286
Sep 5, 2026$288
Sep 6, 2026$288
Sep 7, 2026$278
Sep 8, 2026$261
Sep 9, 2026$261
Sep 10, 2026$261
Sep 11, 2026$267
Sep 12, 2026$284
Sep 13, 2026$284
Sep 14, 2026$284
Sep 15, 2026$284
Sep 16, 2026$284
Sep 17, 2026$284
Sep 18, 2026$284
Sep 19, 2026$293
Sep 20, 2026$293
Sep 21, 2026$293
Sep 22, 2026$284
Sep 23, 2026$275
Sep 24, 2026$275
Sep 25, 2026$275
Sep 26, 2026$276
Sep 27, 2026$284

Google Flights price history returned through Scrapingdog for the dates and settings above. It is not a destination-wide average or a prediction. Source checked Sep 27, 2026.

THE FLIGHT IS ONLY PART OF THE TRIP

Arriving in Guadalajara.

Airport context and source-backed details to help you compare the whole journey.

GDL · Guadalajara International Airport

Guadalajara, Mexico · Airport coordinates 20.523, -103.310

Lowest sample to GDL: $284 round trip from ORD, Jan 23–Jan 30. Different arrival airports may use different dates.

Airport information

Which Guadalajara airports are included?

This page searches GDL — Guadalajara International Airport. Airport coverage follows the destination city market in the passenger dataset, with minor airports excluded. Always check the airport code on both legs: a city search can include different arrival airports, and the cheapest option may not be closest to where you are staying.

Read the source

Why this route is in our research

BTS recorded 238,837 scheduled passengers departing O’Hare and Midway for this destination city market from 2025-07 to 2026-06. That puts it at number 55 in our selected ranking. These are historical on-flight market passengers, not unique travelers, current flight frequencies or a measure of search popularity.

Read the source

Check the location before choosing GDL

The airport reference places Guadalajara International Airport in Guadalajara, Mexico, at 20.523°, -103.310°. Use the airport’s official information to plan your arrival and return journey. Our fare table compares air travel only; ground transfers, luggage and accommodation can change the total trip budget.

Read the source
FLIGHT FOUND. ADVENTURE NEXT.

Make a trip of Guadalajara.

Keep an eye on the whole travel budget, from your first night to your last mile.

A good stay. A happy budget.

Compare places to stay in Guadalajara. Add your dates, check the location, and compare the final total and cancellation terms.

Explore Guadalajara stays ↗Booking.com · choose your travel dates

A little freedom to roam.

Planning a drive beyond Guadalajara? Compare rental cars, mileage, deposits and pickup hours. City-only trip? Public transit may suit you better.

Compare rental cars ↗Discover Cars · enter GDL and your dates

These are planning links, not priced offers. Hotel and car availability is checked by the provider. We currently receive no commission from these links.

GOOD QUESTIONS. STRAIGHT ANSWERS.

Before you take off for Guadalajara.

How can I get Chicago to Guadalajara flight deals in my inbox?

Let us do the fare hunting. Our upcoming free newsletter will bring standout Chicago flight finds to your inbox, with travel dates and booking links so you can check the deal quickly. Use the signup panel near the top of this page when signup opens. It's free, and you'll be able to unsubscribe at any time.

What is the cheapest flight to Guadalajara you have recorded?

The lowest seven-night round-trip search fare in our archive is $284, recorded Sep 27, 2026 for ORD to GDL, Jan 23–Jan 30, 2027. Our route archive starts Sep 27, 2026. This is our observed record, not an industry-wide all-time low, a verified booking price or a current offer.

How much are cheap flights from Chicago to Guadalajara?

Our lowest current seven-night sample is $284 round trip for one adult in economy, from ORD to GDL, Jan 23–Jan 30, 2027. It was checked Sep 27, 2026. This is a dated search result, not a guaranteed ticket price; confirm the return and full fare conditions before paying.

Is O’Hare or Midway cheaper for Guadalajara?

For the matched Jan 23–Jan 30, 2027 search, ORD had the lowest sample at $284. The highest and lowest airport fares were $181 apart. That applies to those dates and settings only. Try other matched dates and add your own ground transport cost in the airport calculator above.

Can I fly nonstop from Chicago to Guadalajara?

The current sample includes a nonstop outbound from ORD to GDL on Jan 23, 2027, with a round-trip search fare of $284. Check the return direction separately: a nonstop outbound does not guarantee a nonstop return.

What is the cheapest month to fly to Guadalajara?

The travel-period chart compares only the dates we sampled. It cannot establish the cheapest month of the year. Start with a promising sampled period, then check nearby dates with the same trip length. The separate history chart tracks one specific search over time; it is not a travel calendar.

Which Guadalajara airport should I choose?

This destination market includes Guadalajara International Airport (GDL). Check the exact arrival code on the fare you choose, then compare the onward journey to your accommodation. The arrival section links airport information and our source-backed planning notes.

Will Skyscanner show the same price as Google Flights?

Not necessarily. The buttons open separate searches with matching airports and dates when a dated sample is available. Providers can show different airlines, sellers, baggage rules and live prices. The sampled Google Flights price is never a Skyscanner quote.

Are bags, hotels and rental cars included?

Do not assume bags are included unless the provider explicitly confirms them. Our research shows flight search fares; the accommodation and rental-car links are separate planning tools. Compare the final total, cancellation terms and location before booking any part of the trip.

Answers use the dated research and sources on this page. Read our flight-saving field notes for a broader planning checklist.

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OPEN ABOUT THE NUMBERS

Sources, coverage & limitations.

This page contains 178 current search-result observations across 24 airport/date searches. Route research is compiled by the Chicago Flight Research desk from the sources below.

Destination photography: photographer, source and reuse license. Airline logos identify the carriers shown in results; no partnership is implied.

BTS demand period: 2025-07 to 2026-06. Searches use one adult, economy, USD and the US market. We do not sell tickets, guarantee fares, or infer baggage inclusions. Read the full methodology